Hydroxy-containing compounds are useful as medicines. However, their reactivity can cause difficulties in their synthesis. Thiadiazoles are also useful in medicinal chemistry. Because of the complex mechanism involved, there exists high variability in the preferred conditions for alternative synthesis of thiadiazoles. Protected glyceraldehydes are valuable chiral starting materials. However they are plagued by their instability.
PCT publications WO09/042435 and WO07/117381 describe an in situ process of preparing substituted thiadiazoles from activated thiocyanates. Amino-substituted thiadiazoles prepared from the acyl thioisocyanates is described in JP4144978.
Althoff et al. [Archiv. der Pharmazie 314, 1981, p 518-524] describe the preparation of related bisulfite adducts from the corresponding cyano dioxolanes. Schmid, C. R. et al [J. Org. Chem, 1991, 56, 4056-4058] describe the preparation of (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde.
There is an ongoing need for more facile and higher yielding processes for preparing such protected glyceraldehydes and thiadiazoles.